Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction

Masayuki Utsugi, Yasuaki Kamada, Hidetoshi Miyamoto, Masahisa Nakada

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction is described. A conjugate addition of cyanide to enone 17 proceeded diastereoselectively to provide the desired 18 incorporating the correct C3 stereogenic center in the taxol C-ring. The intramolecular B-alkyl Suzuki-Miyaura coupling reaction of 22, which was derived from 18, successfully furnished the taxol B-ring in 81% yield.

Original languageEnglish
Pages (from-to)6868-6872
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number39
DOIs
Publication statusPublished - 2007 Sep 24

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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